The grand pink lady on the corner of Oak Bluff’s main thoroughfare is a colorful landmark. It’s trimmed in aqua blue and features a turret-like tower and wrap-around porch full of white wicker rockers and armchairs. It’s a fun place to relax and watch people go by on bustling Circuit Avenue. Inside are lovely hardwood floors and a winding staircase leading up to the top two floors. More comfortable wicker furniture and antiques fill the pantry, dining, and living room areas. This quaint and cozy space invites guest interaction during breakfast and throughout the day. Guitars rest in a corner near a floral-print sofa and two green velour armchairs. A large flat-screen TV shows HBO movies, and magazines rest atop a wooden coffee table. A small, peaceful garden area with tables and chairs is surrounded by greenery. This is a friendly and casual yet quiet place to enjoy the island lifestyle. Guests are mostly couples here, along with some families and traveling friends, here and there. 

The Inn is at the top of Circuit Avenue, the main street running through Oak Bluffs. There are two restaurants directly across the street, as well as Martha’s Vineyard Yoga Center. Other restaurants, shops, and art galleries line the street and are walkable in one to four minutes. A bus stop is only a four-minute walk away, too. The oceanfront at Inkwell Beach is about a five-minute walk through a quiet residential area characterized by the island’s iconic gingerbread houses. Waban Park is a seven-minute walk, as is the historic Flying Horses carousel. But other sights require a car. Joseph Sylvia State Beach and the Farm Neck Golf Club are six-minute drives. Correllus State Forest is 15 minutes away by car. The Oak Bluffs Marina where ferries arrive and depart is an eight-minute walk or about three minutes by car. Martha’s Vineyard Airport is a 15-minute drive or about 30 minutes by bus. 

Oak Bluffs Inn's guest rooms are all air-conditioned and individually decorated. Most are adorned with white Italian bedding and walls painted in muted earth tones. Some have solid-color or print bed throws, and matching bed skirts are typical. Rooms either have simple, earth-tone carpet or plank hardwood floors and quality rugs. Nice period antiques such as desks, poster beds, and armoires are typical, and some rooms have mission-style furnishings. Artwork is traditional and varied, including nautical themes and nature or wildlife depictions. Size and configuration also vary significantly, although most rooms are on the small side but comfortable nevertheless. Most rooms have queen-size beds, but a few have two doubles. Rooms in the carriage house, which includes a two-bedroom apartment with a living room, have private entrances. Bathrooms in most rooms are small and simple, with tile floors and painted walls. Some have shower inserts, and others have shower/tub combos framed with tile walls. Hairdryers and toiletries are provided. Rooms are mostly quiet, but some noise can be heard from street-facing rooms in the main building, and guests on the first floor sometimes can hear guests above them. White-noise machines are a nice touch, as are the iPod dock alarm clocks. All rooms have free Wi-Fi as well. 

Oak Bluffs Inn has several freebies that add to its comfort and value. The daily continental breakfast is included in room rates and features basics like bagels, cereal, yogurt, fruit, and hard-boiled eggs, and a daily changing option, such as scones, banana bread, or bread pudding. And free afternoon snacks include fresh-baked cookies. The kitchen area has a 24/7 pantry with a Keurig coffeemaker and fresh snacks and beverages including free beer, sherry, and port. Guests can also store items in the kitchen’s full-size refrigerator and use the microwave. The Inn provides beach towels, chairs, umbrellas, and coolers for beach-bound guests. The innkeepers also can help arrange island tours and other activities. The living room area has cable TV including HBO, and free Wi-Fi is accessible throughout the property. The Inn has a small library of novels, guidebooks, and other readable material for guest use. There's free off-street parking in a gravel lot framed by a pink fence, with plants, trees, and flowers all around. Be aware that there's no elevator to the second or third floors.